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Compound Detail

CHEMBL253275

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O=C(N[C@@H]1CCOC[C@@H]1C(=O)NO)c1ccc(Cn2c(C(F)(F)F)nc3ccccc32)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL253275
Phase Preclinical
Structure Type MOL
InChI Key PGVYYPZKXKGBLD-JKSUJKDBSA-N
6
Targets
10
Activities
2
Assay Types
17
PK Parameters
20
Publications
0
Known Names

Molecular Properties

462.4
MW (Da)
2.74
ALogP
6
HBA
3
HBD
105.5
PSA (Ų)
0.40
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C22H21F3N4O4
MW 462.43
Aromatic Rings 3
Heavy Atoms 33
NP-Likeness -1.09

Activity Summary

IC50 6 meas. best 8.85
Ki 4 meas. best 6.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Disintegrin and metalloproteinase domain-containing protein 17
CHEMBL3332
 IC50 8.85 8.85 1.4 2
Disintegrin and metalloproteinase domain-containing protein 17
CHEMBL3706
 IC50 6.89 6.89 130.0 1
Blood
CHEMBL613416
 IC50 6.63 6.63 232.0 1
A disintegrin and metalloproteinase with thrombospondin motifs 5
CHEMBL2285
 Ki 6.0 5.86 1000.0 2
A disintegrin and metalloproteinase with thrombospondin motifs 4
CHEMBL2318
 Ki 5.17 5.17 6700.0 2
Macrophage metalloelastase
CHEMBL4393
 IC50 5.1 5.1 8000.0 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 3167.18 ng.hr.mL-1 Rattus norvegicus
AUC 2700.59 ng.hr.mL-1 Rattus norvegicus
AUC 4609.04 ng.hr.mL-1 Canis lupus familiaris
AUC 18252.11 ng.hr.mL-1 Canis lupus familiaris
CL 26.67 mL.min-1.kg-1 Rattus norvegicus
CL 10.0 mL.min-1.kg-1 Canis lupus familiaris
F 53.0 % Rattus norvegicus
F 99.0 % Canis lupus familiaris
Fu 0.2 - Rattus norvegicus
Fu 0.2 - Canis lupus familiaris
Fu 0.21 - Homo sapiens
T1/2 3.5 hr Rattus norvegicus
T1/2 2.4 hr Rattus norvegicus
T1/2 4.2 hr Canis lupus familiaris
T1/2 4.8 hr Canis lupus familiaris
Tmax 0.3 hr Rattus norvegicus
Tmax 0.5 hr Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Disintegrin and metalloproteinase domain-containing protein 17 IC50 = 1.4 nM 8.85 Inhibition of semi purified pig TACE 18242982
Disintegrin and metalloproteinase domain-containing protein 17 IC50 = 1.4 nM 8.85 Inhibition of pig TACE 18790648
Disintegrin and metalloproteinase domain-containing protein 17 IC50 = 130.0 nM 6.89 Inhibition of TACE in human whole blood assessed as reduction of of LPS-induced ... 21963348
Blood IC50 = 232.0 nM 6.63 Reduction of LPS-induced TNFalpha in human whole blood 18242982
A disintegrin and metalloproteinase with thrombospondin motifs 5 Ki = 1000.0 nM 6.0 Inhibition of ADAMTS5 18242982
A disintegrin and metalloproteinase with thrombospondin motifs 5 Ki = 1900.0 nM 5.72 Inhibition of ADAMTS5 18790648
A disintegrin and metalloproteinase with thrombospondin motifs 4 Ki = 6700.0 nM 5.17 Inhibition of ADAMTS4 18242982
A disintegrin and metalloproteinase with thrombospondin motifs 4 Ki = 6700.0 nM 5.17 Inhibition of ADAMTS4 18790648
Macrophage metalloelastase IC50 = 8000.0 nM 5.1 Inhibition of MMP12 18242982
Macrophage metalloelastase IC50 = 8000.0 nM 5.1 Inhibition of MMP12 18790648

Literature References

PubMed DOI Target Context # Activities
18242982 10.1016/j.bmcl.2008.01.075 Canis familiaris 8
18242982 10.1016/j.bmcl.2008.01.075 Rattus norvegicus 8
18242982 10.1016/j.bmcl.2008.01.075 Serum 3
21963348 10.1016/j.ejmech.2011.09.018 Disintegrin and metalloproteinase domain-containing protein 17 3
18242982 10.1016/j.bmcl.2008.01.075 Stromelysin-2 1
18242982 10.1016/j.bmcl.2008.01.075 A disintegrin and metalloproteinase with thrombospondin motifs 5 1
18242982 10.1016/j.bmcl.2008.01.075 A disintegrin and metalloproteinase with thrombospondin motifs 4 1
18242982 10.1016/j.bmcl.2008.01.075 A disintegrin and metalloproteinase with thrombospondin motifs 1 1
18242982 10.1016/j.bmcl.2008.01.075 Matrix metalloproteinase-16 1
18242982 10.1016/j.bmcl.2008.01.075 Matrix metalloproteinase-14 1
18242982 10.1016/j.bmcl.2008.01.075 Collagenase 3 1
18242982 10.1016/j.bmcl.2008.01.075 Macrophage metalloelastase 1
18242982 10.1016/j.bmcl.2008.01.075 Disintegrin and metalloproteinase domain-containing protein 17 1
18242982 10.1016/j.bmcl.2008.01.075 Neutrophil collagenase 1
18242982 10.1016/j.bmcl.2008.01.075 Matrilysin 1
18242982 10.1016/j.bmcl.2008.01.075 Stromelysin-1 1
18242982 10.1016/j.bmcl.2008.01.075 Caco-2 1
18242982 10.1016/j.bmcl.2008.01.075 Matrix metalloproteinase-9 1
18242982 10.1016/j.bmcl.2008.01.075 72 kDa type IV collagenase 1
18242982 10.1016/j.bmcl.2008.01.075 Interstitial collagenase 1

Data from ChEMBL 36 via Core Engine